Antisocial adults exhibit a life-course persistent pattern of conduct problems (CP) with roots in early childhood, including evidence for precursors dating to infancy. A specific aspects of psychopathy, namely callous and unemotional (CU) traits, has been identified as an additional risk factor for young children with conduct problems. Children with conduct problems and CU traits (CP+CU) differ from those without CU traits on behavioral, emotional, biological, cognitive, and developmental measures. Furthermore, children with CP+CU typically exhibit more severe and violent antisocial behavior that is more like to persist over time. The etiology of CU and CP+CU, however, is still relatively unknown. Whereas negative parenting is an established risk factor for the development of CP, the roles of parenting and early relational experience is less understood for children with CU. In addition, although there has been research on early attachment quality and later CP, to date there has been no large-scale investigation of early attachment and later CU or CP+CU, despite evidence that disorganized attachment quality is a risk factor for maladaptive behavioral outcomes well into adolescence and adulthood. This proposal is unique from previous research in two important domains. First, this proposal will utilize observed measures of parenting and attachment, including normative variations in parenting (maternal insensitivity), non-normative parenting (atypical caregiving), and observed attachment quality from the Strange Situation Paradigm. Previous studies examining CP, CU, and CP+CU have largely relied on parent-report of caregiving behaviors. Second, to our knowledge this would be one of the first studies to examine caregiving and relational antecedents of CU and CP+CU during the first years of life. This is a critical developmental period for the acquisition of self-regulatory and empathetic functioning, deficits of which have been associated with CP, CU, and CP+CU. In this proposal we argue that unique dimensions of parenting behavior and early attachment relationships may differentially predict children with CP, CU and CP+CU from normative controls. These hypotheses include main effects for maternal insensitivity, atypical parenting, and attachment quality, as well as the prediction that attachment insecurity may result in heightened child susceptibility to the effects of insensitivity and atypical parenting, rendering children from these caregiving and attachment backgrounds most vulnerable for later CP, CU and CP+CU. To test these hypotheses we will utilize the longitudinal dataset on maternal sensitivity, attachment quality, and child behavior outcomes provided by the NICHD Study of Early Child Care and Youth Development (SECCYD). In addition to secondary data analyses, we will recode a subsample of SECCYD parent-child interactions for coding atypical maternal behaviors. The SECCYD is one of the few studies with longitudinal data and a sample size large enough to test these hypotheses. Furthermore, because this proposal focuses largely on secondary data analyses, it is a cost efficient means of addressing questions of significant scientific and societal importance.